MRI Related Reagents – ChemiMart

DOTA-Biotin-Sarcosine

mzaug — Wed, 09 Dec 2020 15:05:17 +0000

Other names: 1-(5-Hydroxyindole-3-ethylacetamide)-4,7,10-triacetic acid-1,4,7,10-tetraazacyclododecane. [3aS-[3aα,4β(R*),6aα]]-2-[[4-[[[[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]methylamino]acetyl]amino]phenyl]methyl]-1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid.

DOTA-conjugate with biotin through a sarcosine linker.

This product is a ligand for the preparation of the imaging Gd-complex. It can be used as an activatable paramagnetic imaging agent. The biotin motif is a popular linker used in biotechnology to conjugate proteins for biochemical assays. Both streptavidin and avidin bind with biotin with high affinity and specificity, thus allowing target visulalization by MRI using biotinilated Gd-DOTA reagent.

Ref.:

1) MRI Contrast Agents: From Molecules to Particles.

S. Laurent, C. Henoumont, D. Stanicki, S. Boutry, E. Lipani, S. Belaid, R.N. Muller, L.V. Elst, ISSN 2191-530X, 2017.

DOI: 10.1007/978.981.10.2529.7

2) Recent development of biotin conjugation in biological imaging, sensing, and target delivery.

W.X. Ren, J. Han, S. Uhm, Y.J. Jang, C. Kang, J.-H. Kim, J. S. Kim, Chem. Comm. 2015, 51, 10403-10418.

DOI: 10.1039/C5CC03075G

3) Target Visualization by MRI Using the Avidin/Biotin Amplification Route: Synthesis and Testing of a Biotin–Gd‐DOTA Monoamide Trimer.

L. Tei, A. Barge, S.G. Crich, R. Pagliarin, V. Negri, D. Ramella, G. Cravotto, S. Aime, Chemistry 2010, 16, 8080-8089.

DOI: 10.1002/chem.201000508

DO3A-Serotonine, 5-HT-DOTAGA

mzaug — Wed, 09 Dec 2020 15:02:30 +0000

Other names: 5-HT-DOTA, 1-(5-Hydroxyindole-3-ethylacetamide)-4,7,10-triacetic acid-1,4,7,10-tetraazacyclododecane; DOTA-conjugate with serotonine.

This product is a ligand for the preparation of the imaging Gd-complex. It can be used as an activatable paramagnetic imaging agent to directly image myeloperoxydase (MPO). Secrecretion of MPO by activated macrophages and neutrophils in humans found to be in correlation with plaque rupture in atherosclerotic disease, that is the major cause of morbidity.

Ref.:

1) MRI Contrast Agents: From Molecules to Particles.

S. Laurent, C. Henoumont, D. Stanicki, S. Boutry, E. Lipani, S. Belaid, R.N. Muller, L.V. Elst, ISSN 2191-530X, 2017.

DOI: 10.1007/978.981.10.2529.7

2) High-resolution Imaging of Myeloperoxidase Activity Sensors in Human Cerebrovascular Disease.

Y.Z. Wadghiri, D.M. Hoang, A. Leporati, M.J. Gounis, A. Rodríguez-Rodríguez, M.L. Mazzanti, J.P. Weaver, A.K. Wakhloo, P. Caravan, A.A. Bogdanov Jr, Sci Rep 2018, 8, 7687. Open Access

DOI: 10.1038/s41598-018-25804-y

NO2A-(t-Bu ester)

mzaug — Wed, 09 Dec 2020 14:59:24 +0000

Other names: 1,4,7-Triazacyclononane-1,4-bis(t-butyl acetate). tert-Butyl 2-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7-triazonan-1-yl]acetate.

This product is a building block that can be used for example in the preparation of metal chelates for imaging applications in biological objects.

Ref.:

1) ⁶⁴Cu-NO2A-RGD-Glu-6-Ahx-BBN(7-14)NH2: a heterodimeric targeting vector for positron emission tomography imaging of prostate cancer.

A.B. Jackson, P.K. Nanda, T.L. Rold, G.L. Sieckman, A.F. Szczodroski, T.J. Hoffman, X. Chen, C.J. Smith, Nucl. Med. Biol. 2012, 39, 377–387.

DOI: 10.1016/j.nucmedbio.2011.10.004

2) Ga[NO2A-N-(α-amino)propionate] chelates: synthesis and evaluation as potential tracers for ⁶⁸Ga PET.

M.F.Ferreira, G. Pereira, J.P. André, M.I. Prata, P.M. Ferreira, J.A. Martins, C.F. Geraldes, Dalton Trans. 2014, 43, 8037-8047.

DOI: 10.1039/c4dt00386a.

Tris-BOC-Cyclen

mzaug — Wed, 09 Dec 2020 14:56:24 +0000

Other name: N,N′,N′′-Tri-Boc-cyclen. 1,4,7-Tri-Boc-1,4,7,10-tetraazacyclododecane.

This product is a very important intermediate in the synthesis of the mono-N-functionalized DOTA-based ligands.

Ref.:

1) Biomedical Imaging: The Chemistry of Labels, Probes and Contrast Agents. Chapter 5.2

M. Braddock, Royal Society of Chemistry, 23.11.2011

2) A Tris(Zn^II−1,4,7,10-tetraazacyclododecane) Complex as a New Receptor for Phosphate Dianions in Aqueous Solution.

E. Kimura, S. Aoki T. Koike, M. Shiro, J. Am. Chem. Soc. 1997, 119, 3038-3076.

DOI: 10.1021/ja9640408

Maleimido-mono-amide-DOTA-tris (t-Bu ester)

mzaug — Wed, 09 Dec 2020 14:53:51 +0000

Other names: MMA-DOTA. 1,4,7,10-Tetraazacyclododecane-1,4,7-tris-tert-butyl acetate-10-maleimidoethylacetamide.

This product can be used for the preparation of metal complexes for MRI applications. Specific reactivity toward thiol-groups allows labeling of peptides and other biomolecules under mild conditions.

Ref.:

1) Evaluation of Maleimide Derivative of DOTA for Site-Specific Labeling of Recombinant Affibody Molecules.

S. Ahlgren, A. Orlova, D. Rosik, M. Sandström, Bioconjugate Chem. 2008, 19, 235-243.

DOI: 10.1021/bc700307y

2) Pre-labelling versus direct labelling of anthrax proteins for imaging of matrix metalloproteinases activity using DOTA-GA.

M.-A. Elvina Xavier, S. Liu, S.H. Leppla, B. Cornelissen, Nucl. Med. Biol. 2019, 72-73, 49-54.

DOI: 10.1016/j.nucmedbio.2019.07.007

p-SCN-Bn-TCMC

mzaug — Wed, 09 Dec 2020 14:45:23 +0000

2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraaza-1,4,7,10-tetra(2-carbamoylmethyl)cyclododecane.

This product is a modified DOTA-chelator containig isothiocyanate functional group and reactive towards various nucleophiles including amine and sulfhydryl groups on proteins.

Ref.:

1) Preparation of ²¹²Pb-labeled monoclonal antibody using a novel ²²⁴Ra-based generator solution.

S. Westrøm, R,Generalov, T.B. Bønsdorff, R.H. Larsen Nucl. Med. Biol. 2017, 51, 1-9.

DOI: 10.1016/j.nucmedbio.2017.04.005.